Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 15, Problem 15.41SP
An important variation of the Diels-Alder reaction is intramolecular, in which the diene and the dienophile are connected. This type of Diels-Alder reaction makes two new rings. Draw the compound produced in each of these examples; try to predict stereochemistry (using models will help). In some cases, Lewis acid catalysts are used; that can be ignored for this problem.
Prof. H. Miyaoka, Tokyo U. Synthesis Letters, 2011, 547. (R and R2 are different alkyl groups.)
Prof. A. Kirschning, Leibnitz U. Hannover Organic Letters, 2014, 16, 568. (Ar1 and Ar2 are different aryl groups.)
Prof. H. Zhai, Lanzhou U. Organic Letters, 2014, 16, 216.
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the given copies of the starting materials to draw the major product(s) for the following Diels-Alder reaction. Use the
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Refute or Defend: Once cyclopentadiene is distilled, it can be stored for a long period of time (e.g., weeks) before using it in a Diels-Alder reaction
Imagine that you used isoprene as diene – in that case you don’t have to worry about assigning endo vs exo. Draw the "endo" and "exo" products of the Diels-Alder reaction between isoprene and maleic anhydride, and explain why the distinction is irrelevant here.
Chapter 15 Solutions
Organic Chemistry (9th Edition)
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
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- 3.arrow_forwardThe below reaction is a retro Diels-Alder reactions. Is is the reverse process of a Diels-Alder reaction with the formation of a diene and dienophile from some cyclohexene. It can be accomplished spontaneously with heat. Determine the product of the reaction. 4 Heatarrow_forwardDraw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown CH3CH2O. Diene + Dienophile Co,CH3 •Consider E Z stereochemistry of alkenes. •Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the sign from the drop-down menu. C. P. opy aste %3Darrow_forward
- In Section 24.5, we learned how to use resonance OCH3 hybrids to understand the regiochemistry of Diels-Alder reactions. Frontier MO theory, on the other hand, explains the regiochemistry by taking into account the extent of orbital overlap between the frontier MOs. Consider the diene and dienophile shown here having the two different approaches indicated. In both cases, the p orbital contributions are shown for the pertinent frontier MOs. The relative contributions by the p AOs to the frontier MOs are indicated by the p AO sizes. Use this information to explain which approach is favored. CH30 LOCH3arrow_forwardModify the given copies of the starting material to draw the major products for the following Diels-Alder reaction. Use the single bond to go to enter, convert between double and single bonds, and use wedges and dashes to indicate the stereochemistry of any newly formed chiral centers. Include minor product(s) if any as well pleasearrow_forwardDo Theoretical Yield Reaction and Calculation Table (balanced equation, formula, moles, molecular weight, grams, etc.) for hydrolysis of the Diels-Alder Anhydride Product. Attached is what I have tried to do so far.arrow_forward
- Organic Chemistryarrow_forward1) In the Diels-Alder reaction there are two reaction components: a DIENE (must be a conjugated diene); and a DIENOPHILE (an ene usually with electron withdrawing substituents). a. Bicyclic diene A reacts readily with appropriate alkenes by the Diels-Alder reaction, whereas diene B is totally unreactive. Explain. b. Write the three reactions and show the product for diene A reacting with dienophiles I, II, and III. Rank I, II, and III in terms of their expected reactivity in a Diels Alder reaction. Justify your assigned ranks. A B || LOCH3 IIIarrow_forwardFollowing is an example of a type of reaction known as a Diels-Alder reaction 1,3-Pentadiene Ethylene 3-Methylcyclohexene (a racemic mixture) The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is one of the few ways that chemists have to form two new carbon-carbon bonds in a single reaction. Given what you know about the relative strengths of carbon-carbon sigma and pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic? Explain your reasoning.arrow_forward
- Note:- • Do not provide handwritten solution. Maintain accuracy and quality in your answer. Take care of plagiarism. • Answer completely. • You will get up vote for sure.arrow_forwardWhich of the following structures, A or B, has the faster rate of reaction in a Diels-Alder reaction? Give a brief explanation that includes the terms "donating group", "withdrawing group", "energy of the electrons", "HOMO". H :0: A H₂N. Barrow_forward[Review Topics] [References] Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. Diene + Dienophile CH3O CH₂ I wwwwwwwarrow_forward
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